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From 1967 to 1970, Smallwood served in the United States ArmyAirborne Infantry. Commanding a Mobile Advisory Team during the Vietnam War, he was wounded in action. After recovering from the injuries, Smallwood moved to New York City where he studied acting at the Neighborhood Playhouse and established a career as a performer in Broadway productions (Mahalia), films and television.

He often plays military characters, and as a science fiction fan, he always longed to play a Star Trek alien. He came close on Voyager when he played the human form of a disguised alien, but it was not until Enterprise that he played a fully alien character, a sympathetic Xindi, for several episodes.

Smallwood sometimes sings in his acting roles. He plays his guitar on several occasions on Space: Above and Beyond, as Commodore Ross. His character on Millennium sang to people before euthanizing them. He is the vocalist in the blues band Incarnation with guitarist Arlen Roth. Their self-titled first album, produced in 1994 at Clark Dimond's Dimond Studio in Colorado's Sangre de Cristo Mountains, is a tribute to the music of Delta Blues King Robert Johnson with 15 tracks written by or associated with Johnson.

He is the author of Return To Eden, anthology of 33 personal essays describing his tour of duty in Vietnam, his life as performer and his return to Vietnam in 2004. Some of these essays previously appeared in magazines. In 2006, the mp3 version of Return to Eden was first runner-up in the audio/spoken word category at the Fifth Annual DIY Book Festival, which celebrates independent authors and publishers.[1] In 2009 he hosted the hybrid television radio horror anthology series As Darkness Falls.[2]